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Former President Donald Trump has repeatedly shown his desire to see critics investigated, exerting influence on the Justice Department to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our reputation and trustworthiness," the leader stated last month in a Truth Social post.

"They impeached me, and indicted me (5 times!)" he declared, referencing the four criminal cases he encountered after departing the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in cases that many experts have stated appear to be politically motivated and difficult to succeed in court.

But the most recent charges against a presidential opponent, former national security adviser John Bolton, differ significantly, legal experts and ex-prosecutors say.

"In my opinion, contrasting Bolton's charges to James' is like comparing two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Details of the Legal Situation

Bolton has been criminally indicted on national allegations pertaining to the supposed mishandling of sensitive materials. After departing the White House in 2019, he has become a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Specialists contend that while there may be political reasons to target Bolton, the methods used to obtain an indictment and the proof compiled against him indicate a possibly more substantial case than the DOJ brought against James.

"This misconduct that's being claimed is simultaneously more serious and appears to have taken place over a significant period of time," commented Carissa Byrne Hessick, a professor at the University of North Carolina School of Law.

Throughout his time as Trump's security advisor, and after his 2019 White House exit, prosecutors alleged that Bolton put the country at risk by wrongfully keeping and transmitting classified information to relatives using unprotected methods, including AOL. Some of the materials were labeled top secret.

The charge states that at one point a hacker gained access to Bolton's system where files were kept and transmitted an seeming threat to cause "the largest scandal since Hillary [Clinton]'s emails were released".

Bolton entered a not guilty plea during a court appearance on Friday to eighteen separate counts of improperly handling sensitive materials.

Political Motivation or a Strong Legal Argument?

The schedule of his indictment - coming on the heels of charges against James - has renewed questions about external influence on the justice system.

Trump previously suggested Bolton belonged in jail, and described him a "sleazebag". Bolton, for his role, authored a book about his time in the Trump government that was highly critical of the president.

"There's no question that the timing of this charge, when paired with additional cases, has raised questions about the validity of these allegations, and the reason these counts are being brought now," said Jamil Jaffer, founder and director of the National Security Institute.

Nevertheless, he continued, "if the Justice Department is capable to demonstrate the allegations stated and show the information is correctly classified, his conduct may very well have violated the law".

Prosecuting such a senior official for mishandling classified documents is "rare" but not unprecedented, noted Carrie Cordero, a expert at the Center for a New American Security.

"Situations that concern sensitive materials present challenges to prosecute, but they may and are brought against both junior and high-level officials, from time to time," she explained.

Parallels to Examinations into Former President and President

Trump likewise faced charges of wrongfully storing classified documents at his Mar-a-Lago resort in Florida and hindering their return, but that case was ultimately thrown out by a federal judge and negated by his return as president.

A independent investigator additionally found that former President Joe Biden improperly stored sensitive materials from his period as second-in-command, but did not criminally charge him.

Bolton's case shares characteristics to Trump's sensitive materials matters, said Mr Lesko, who also held a top security role at the DOJ.

Strict procedures regulate the handling of sensitive materials. To win a guilty verdict, the government must prove that Bolton was aware the material he was sending was classified, and he had to knowingly transmit it to someone without authorization to obtain it.

"Because of the classified nature of the information at issue in this case, we don't have a lot of particulars about why the prosecution contends elements like the personal notes and the additional information he shared by email, and the reason there were restricted," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the DOJ initiated this legal action will be under scrutiny, after Trump openly expressed his desire to see his political opponents charged and some of those indictments materialized.

But Mr Lesko said in Bolton's case, authorities appear to have followed standard procedure.

"This Bolton case and ultimately the charge seemed to have observed the regular procedure including the rules and standards within the DOJ," he said.

In contrast to Comey's brief, two-page charge, Bolton's was a more "traditional" document that "explicitly outlines the particulars involving the facts and situation here," Mr Lesko commented.

"It seems fairly aligned with a series of cases... where government officials mishandled and shared sensitive information."